Ethyl 2-(5-fluoro-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536809025938

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1826

doi:10.1107/S1600536809025938

Open

access

Ethyl 2-(5-fluoro-3-methylsulfinyl-1-benzofuran-2-yl)acetate

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 1 July 2009; accepted 4 July 2009; online 11 July 2009)

In the title compound, C₁₃H₁₃FO₄S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The crystal structure exhibits four intermolecular non-classical C—H⋯O hydrogen bonds. In addition, the crystal structure contains aromatic π–π interactions between the furan and benzene rings of adjacent molecules [centroid–centroid distance = 3.743 (2) Å], and two intermolecular C—H⋯π interactions.

Related literature

For the crystal structures of similar ethyl 2-(5-halo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2007a ,b ,c ). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ); Twyman & Allsop (1999 ).

Experimental

Crystal data

C₁₃H₁₃FO₄S
M_r = 284.29
Triclinic, $[P \overline 1]$
a = 7.8821 (5) Å
b = 9.0922 (5) Å
c = 10.4354 (6) Å
α = 73.682 (1)°
β = 79.155 (1)°
γ = 66.622 (1)°
V = 656.31 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 273 K
0.40 × 0.40 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
5673 measured reflections
2805 independent reflections
2512 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.04
2805 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4ⁱ	0.93	2.42	3.3374 (19)	168
C5—H5⋯O3ⁱⁱ	0.93	2.67	3.482 (2)	147
C9—H9A⋯O4ⁱⁱⁱ	0.97	2.21	3.177 (2)	172
C9—H9B⋯O1^iv	0.97	2.59	3.542 (2)	169
C11—H11A⋯Cg2^v	0.97	2.92	3.773 (2)	148
C12—H12C⋯Cg1^v	0.97	2.81	3.502 (2)	129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) -x+2, -y+1, -z+1; (iv) -x+2, -y+1, -z+2; (v) x, y+1, z.Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025938/ez2175sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025938/ez2175Isup2.hkl

checkCIF report

Comment top

Molecules containing the benzofuran ring system have attracted considerable interest in view of their biological and pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999). This work is related to our communications on the synthesis and structures of ethyl 2-(5-halo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, viz. ethyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2007a), ethyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl) acetate (Choi et al., 2007b), and ethyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2007c). Here we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The crystal packing (Fig. 2) exhibits weak intermolecular C–H···O non-classical hydrogen bonds; the first between an H atom of the benzofuran ring and the S═O unit, with a C3–H3···O4ⁱ, the second between an H atom of benzofuran ring and the C═O unit, with a C5-H5···O3ⁱⁱ, the third between an H atom of the methylene group bonded to carboxylate C atom and the S═O unit, with a C9–H9A···O4ⁱⁱⁱ, the fourth between an H atom of the methylene group bonded to carboxylate C atom and the furan O atom, with a C9–H9B···O1^iv, respectively (Table 1 and Fig. 2). Additionally, the crystal packing (Fig. 3) contains aromatic π–π interactions between the furan and the benzene rings of the neighbouring molecules, with a Cg1···Cg2^vi distance of 3.743 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2-C7 benzene ring, respectively). The molecular packing is further stabilized by two intermolecular C–H···π interactions; the first between the methylene H atom of ethoxy group and the benzene ring of a neighbouring molecule (C11–H11A···Cg2^v), the second between the methyl H atom of ethoxy group and the furan ring of a neighbouring molecule (C12–H12C···Cg1^v), respectively (Table 1 and Fig. 3).

Related literature top

For the crystal structures of similar ethyl 2-(5-halo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2007a,b,c). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999).

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

Experimental top

77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of ethyl 2-(5-fluoro-3-methylsulfanyl-1-benzofuran-2-yl)acetate (268 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 4 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate,1:2 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 401-402 K; R_f = 0.43 (hexane-ethyl acetate, 1;2 v/v )]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small cycles of arbitrary radius.
	Fig. 2. The C–H···O interactions (dotted lines) in the title compound. [Symmetry code: (i) - x + 1, - y + 1, - z + 1; (ii) - x + 1, - y + 1, - z + 2; (iii) - x + 2, - y + 1, - z + 1; (iv) - x + 2, - y + 1, - z + 2.]
	Fig. 3. The π–π and C–H···π interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry code: (v) x, 1 + y, z; (vi) 1 - x, 1 - y, 2 - z; (vii) 1 - x, 2 - y, 2 - z; (viii) x, - 1 + y, z.]

Ethyl 2-(5-fluoro-3-methylsulfinyl-1-benzofuran-2-yl)acetate top

Crystal data top

C₁₃H₁₃FO₄S	Z = 2
M_r = 284.29	F(000) = 296
Triclinic, P1	D_x = 1.439 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8821 (5) Å	Cell parameters from 4105 reflections
b = 9.0922 (5) Å	θ = 2.5–27.5°
c = 10.4354 (6) Å	µ = 0.27 mm⁻¹
α = 73.682 (1)°	T = 273 K
β = 79.155 (1)°	Block, colourless
γ = 66.622 (1)°	0.40 × 0.40 × 0.10 mm
V = 656.31 (7) Å³

Data collection top

Bruker SMART CCD diffractometer	2512 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.063
Graphite monochromator	θ_max = 27.0°, θ_min = 2.0°
Detector resolution: 10.0 pixels mm^-1	h = −10→10
ϕ and ω scans	k = −11→11
5673 measured reflections	l = −13→13
2805 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: difference Fourier map
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0465P)² + 0.2336P] where P = (F_o² + 2F_c²)/3
2805 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₃H₁₃FO₄S	γ = 66.622 (1)°
M_r = 284.29	V = 656.31 (7) Å³
Triclinic, P1	Z = 2
a = 7.8821 (5) Å	Mo Kα radiation
b = 9.0922 (5) Å	µ = 0.27 mm⁻¹
c = 10.4354 (6) Å	T = 273 K
α = 73.682 (1)°	0.40 × 0.40 × 0.10 mm
β = 79.155 (1)°

Data collection top

Bruker SMART CCD diffractometer	2512 reflections with I > 2σ(I)
5673 measured reflections	R_int = 0.063
2805 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	Δρ_max = 0.40 e Å⁻³
2805 reflections	Δρ_min = −0.35 e Å⁻³
173 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S	0.72668 (5)	0.63168 (5)	0.54574 (3)	0.02919 (13)
F	0.32177 (16)	0.21796 (16)	0.88301 (12)	0.0529 (3)
O1	0.84077 (14)	0.45046 (13)	0.92200 (9)	0.0247 (2)
O2	1.01504 (16)	0.88467 (14)	0.73052 (13)	0.0368 (3)
O3	0.73837 (17)	0.89429 (16)	0.69571 (14)	0.0428 (3)
O4	0.74634 (18)	0.50040 (17)	0.47717 (11)	0.0422 (3)
C7	0.7124 (2)	0.38103 (18)	0.92490 (14)	0.0246 (3)
C1	0.7324 (2)	0.53985 (18)	0.71812 (13)	0.0235 (3)
C2	0.6385 (2)	0.43348 (18)	0.80110 (14)	0.0236 (3)
C3	0.5036 (2)	0.3785 (2)	0.78410 (16)	0.0296 (3)
H3	0.4504	0.4109	0.7035	0.036*
C4	0.4545 (2)	0.2735 (2)	0.89391 (18)	0.0342 (4)
C5	0.5303 (2)	0.2183 (2)	1.01700 (17)	0.0350 (4)
H5	0.4925	0.1450	1.0866	0.042*
C6	0.6629 (2)	0.2741 (2)	1.03413 (15)	0.0301 (3)
H6	0.7157	0.2412	1.1149	0.036*
C8	0.8506 (2)	0.54532 (18)	0.79478 (13)	0.0228 (3)
C9	0.9836 (2)	0.63165 (18)	0.76654 (14)	0.0254 (3)
H9A	1.0746	0.5942	0.6946	0.030*
H9B	1.0489	0.6012	0.8456	0.030*
C10	0.8940 (2)	0.81678 (19)	0.72758 (14)	0.0268 (3)
C11	0.9500 (3)	1.0649 (2)	0.6923 (2)	0.0499 (5)
H11A	0.8265	1.1120	0.7346	0.060*
H11B	0.9456	1.1029	0.5959	0.060*
C12	1.0827 (3)	1.1155 (2)	0.7373 (2)	0.0458 (4)
H12A	1.2045	1.0677	0.6952	0.055*
H12B	1.0850	1.0781	0.8329	0.055*
H12C	1.0441	1.2333	0.7130	0.055*
C13	0.4872 (2)	0.7641 (2)	0.54508 (17)	0.0385 (4)
H13A	0.4622	0.8305	0.4563	0.058*
H13B	0.4603	0.8341	0.6059	0.058*
H13C	0.4108	0.6988	0.5727	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0300 (2)	0.0380 (3)	0.01935 (19)	−0.01155 (17)	−0.00708 (14)	−0.00428 (15)
F	0.0482 (6)	0.0562 (8)	0.0708 (8)	−0.0359 (6)	−0.0137 (6)	−0.0093 (6)
O1	0.0298 (5)	0.0263 (5)	0.0213 (5)	−0.0122 (4)	−0.0090 (4)	−0.0032 (4)
O2	0.0328 (6)	0.0229 (6)	0.0573 (7)	−0.0104 (5)	−0.0141 (5)	−0.0059 (5)
O3	0.0347 (6)	0.0308 (7)	0.0608 (8)	−0.0108 (5)	−0.0202 (6)	0.0016 (6)
O4	0.0430 (7)	0.0561 (9)	0.0291 (6)	−0.0093 (6)	−0.0085 (5)	−0.0218 (5)
C7	0.0259 (7)	0.0238 (7)	0.0261 (7)	−0.0083 (6)	−0.0063 (5)	−0.0073 (5)
C1	0.0262 (7)	0.0247 (7)	0.0208 (6)	−0.0073 (6)	−0.0067 (5)	−0.0065 (5)
C2	0.0241 (7)	0.0229 (7)	0.0245 (7)	−0.0057 (6)	−0.0058 (5)	−0.0082 (5)
C3	0.0274 (7)	0.0308 (8)	0.0346 (8)	−0.0092 (6)	−0.0089 (6)	−0.0118 (6)
C4	0.0297 (8)	0.0324 (9)	0.0480 (9)	−0.0156 (7)	−0.0057 (7)	−0.0126 (7)
C5	0.0360 (9)	0.0291 (8)	0.0397 (9)	−0.0154 (7)	−0.0015 (7)	−0.0035 (7)
C6	0.0349 (8)	0.0271 (8)	0.0275 (7)	−0.0114 (7)	−0.0063 (6)	−0.0024 (6)
C8	0.0259 (7)	0.0219 (7)	0.0209 (6)	−0.0072 (6)	−0.0056 (5)	−0.0050 (5)
C9	0.0248 (7)	0.0252 (8)	0.0275 (7)	−0.0086 (6)	−0.0077 (5)	−0.0052 (5)
C10	0.0285 (7)	0.0274 (8)	0.0258 (7)	−0.0112 (6)	−0.0058 (6)	−0.0043 (6)
C11	0.0485 (11)	0.0228 (9)	0.0790 (14)	−0.0104 (8)	−0.0232 (10)	−0.0047 (9)
C12	0.0414 (10)	0.0269 (9)	0.0701 (13)	−0.0142 (8)	−0.0037 (9)	−0.0109 (8)
C13	0.0342 (8)	0.0366 (10)	0.0365 (9)	−0.0027 (7)	−0.0147 (7)	−0.0031 (7)

Geometric parameters (Å, º) top

S—O4	1.5007 (13)	C5—C6	1.387 (2)
S—C1	1.7583 (14)	C5—H5	0.9300
S—C13	1.7914 (18)	C6—H6	0.9300
F—C4	1.3633 (17)	C8—C9	1.4859 (19)
O1—C8	1.3723 (17)	C9—C10	1.509 (2)
O1—C7	1.3813 (16)	C9—H9A	0.9700
O2—C10	1.3343 (17)	C9—H9B	0.9700
O2—C11	1.466 (2)	C11—C12	1.488 (3)
O3—C10	1.2035 (19)	C11—H11A	0.9700
C7—C6	1.381 (2)	C11—H11B	0.9700
C7—C2	1.3972 (19)	C12—H12A	0.9600
C1—C8	1.3603 (19)	C12—H12B	0.9600
C1—C2	1.446 (2)	C12—H12C	0.9600
C2—C3	1.3984 (19)	C13—H13A	0.9600
C3—C4	1.373 (2)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.396 (2)

O4—S—C1	106.41 (7)	O1—C8—C9	116.26 (11)
O4—S—C13	106.04 (8)	C8—C9—C10	113.99 (12)
C1—S—C13	98.86 (8)	C8—C9—H9A	108.8
C8—O1—C7	106.33 (10)	C10—C9—H9A	108.8
C10—O2—C11	116.58 (13)	C8—C9—H9B	108.8
C6—C7—O1	125.26 (12)	C10—C9—H9B	108.8
C6—C7—C2	124.13 (13)	H9A—C9—H9B	107.6
O1—C7—C2	110.62 (12)	O3—C10—O2	123.99 (15)
C8—C1—C2	107.22 (12)	O3—C10—C9	126.12 (13)
C8—C1—S	122.68 (11)	O2—C10—C9	109.88 (12)
C2—C1—S	129.73 (10)	O2—C11—C12	107.55 (15)
C7—C2—C3	119.44 (13)	O2—C11—H11A	110.2
C7—C2—C1	104.72 (12)	C12—C11—H11A	110.2
C3—C2—C1	135.84 (13)	O2—C11—H11B	110.2
C4—C3—C2	115.78 (14)	C12—C11—H11B	110.2
C4—C3—H3	122.1	H11A—C11—H11B	108.5
C2—C3—H3	122.1	C11—C12—H12A	109.5
F—C4—C3	118.07 (14)	C11—C12—H12B	109.5
F—C4—C5	116.90 (15)	H12A—C12—H12B	109.5
C3—C4—C5	125.04 (14)	C11—C12—H12C	109.5
C6—C5—C4	119.12 (15)	H12A—C12—H12C	109.5
C6—C5—H5	120.4	H12B—C12—H12C	109.5
C4—C5—H5	120.4	S—C13—H13A	109.5
C7—C6—C5	116.48 (14)	S—C13—H13B	109.5
C7—C6—H6	121.8	H13A—C13—H13B	109.5
C5—C6—H6	121.8	S—C13—H13C	109.5
C1—C8—O1	111.11 (12)	H13A—C13—H13C	109.5
C1—C8—C9	132.64 (13)	H13B—C13—H13C	109.5

C8—O1—C7—C6	178.81 (15)	F—C4—C5—C6	−178.60 (15)
C8—O1—C7—C2	−1.02 (16)	C3—C4—C5—C6	1.5 (3)
O4—S—C1—C8	127.12 (13)	O1—C7—C6—C5	179.74 (15)
C13—S—C1—C8	−123.16 (14)	C2—C7—C6—C5	−0.4 (2)
O4—S—C1—C2	−45.00 (15)	C4—C5—C6—C7	−0.8 (2)
C13—S—C1—C2	64.72 (15)	C2—C1—C8—O1	−0.08 (17)
C6—C7—C2—C3	1.0 (2)	S—C1—C8—O1	−173.75 (10)
O1—C7—C2—C3	−179.12 (13)	C2—C1—C8—C9	179.69 (15)
C6—C7—C2—C1	−178.88 (14)	S—C1—C8—C9	6.0 (2)
O1—C7—C2—C1	0.96 (16)	C7—O1—C8—C1	0.67 (16)
C8—C1—C2—C7	−0.53 (16)	C7—O1—C8—C9	−179.15 (12)
S—C1—C2—C7	172.54 (12)	C1—C8—C9—C10	61.4 (2)
C8—C1—C2—C3	179.57 (17)	O1—C8—C9—C10	−118.84 (14)
S—C1—C2—C3	−7.4 (3)	C11—O2—C10—O3	0.1 (2)
C7—C2—C3—C4	−0.4 (2)	C11—O2—C10—C9	178.79 (15)
C1—C2—C3—C4	179.54 (16)	C8—C9—C10—O3	−13.8 (2)
C2—C3—C4—F	179.21 (14)	C8—C9—C10—O2	167.56 (12)
C2—C3—C4—C5	−0.9 (3)	C10—O2—C11—C12	164.80 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.93	2.42	3.3374 (19)	168
C5—H5···O3ⁱⁱ	0.93	2.67	3.482 (2)	147
C9—H9A···O4ⁱⁱⁱ	0.97	2.21	3.177 (2)	172
C9—H9B···O1^iv	0.97	2.59	3.542 (2)	169
C11—H11A···Cg2^v	0.97	2.92	3.773 (2)	148
C12—H12C···Cg1^v	0.97	2.81	3.502 (2)	129

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+1, −z+2; (v) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃FO₄S
M_r	284.29
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.8821 (5), 9.0922 (5), 10.4354 (6)
α, β, γ (°)	73.682 (1), 79.155 (1), 66.622 (1)
V (Å³)	656.31 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.40 × 0.40 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5673, 2805, 2512
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.04
No. of reflections	2805
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.35

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.93	2.42	3.3374 (19)	168.2
C5—H5···O3ⁱⁱ	0.93	2.67	3.482 (2)	147.1
C9—H9A···O4ⁱⁱⁱ	0.97	2.21	3.177 (2)	172.2
C9—H9B···O1^iv	0.97	2.59	3.542 (2)	168.7
C11—H11A···Cg2^v	0.97	2.92	3.773 (2)	147.8
C12—H12C···Cg1^v	0.97	2.81	3.502 (2)	129.4

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+1, −z+2; (v) x, y+1, z.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3832. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o3850. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007c). Acta Cryst. E63, o4081. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383–9384. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1826

doi:10.1107/S1600536809025938

Open

access